Tyramine → HCID 58603364, compound

HRID 14958Notes

Reaction equation

HRID 14958 reaction equation
C(OC([N:8]1[CH:13]([CH3:14])[CH2:12][N:11]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:27]=[CH:26][N:25]=[C:24](Cl)[N:23]=3)[CH:17]=2)[CH2:10][CH:9]1C)=O)(C)(C)C.[NH2:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1>>[CH:10]12[CH2:14][CH:13]([NH:8][CH2:9]1)[CH2:12][N:11]2[CH2:15][C:16]1[CH:17]=[C:18]([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([NH:30][CH2:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=3)[N:23]=2)[CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 5610TyramineHCID 866033254-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-2,6-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58603364HCID 58603364, compound

Procedure

Intermediate 142 was coupled with tyramine following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 402. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.43 (s, 1H) 8.37 (d, 1H) 8.34 (d, 1H) 8.04 (d, 1H) 7.73 (t 1H) 7.65 (d, 1H) 7.17 (d, 2H) 6.69 (d, 2H) 4.62 (s, 2H) 4.19 (d, 2H) 3.92 (d, 2H) 3.63 (t, 2H) 3.23 (d, 2H) 2.94 (t, 2H) 2.61 (d, 1H) 2.37 (d, 1H).

Sources & evidence

ORD record
ord-e229ec74762b44a082a7e4110554eb90
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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